#------------------------------------------------------------------------------
#$Date: 2016-02-20 05:06:23 +0200 (Sat, 20 Feb 2016) $
#$Revision: 176774 $
#$URL: svn://www.crystallography.net/cod/cif/2/20/31/2203138.cif $
#------------------------------------------------------------------------------
#
# This file is available in the Crystallography Open Database (COD),
# http://www.crystallography.net/. The original data for this entry
# were provided by IUCr Journals, http://journals.iucr.org/.
#
# The file may be used within the scientific community so long as
# proper attribution is given to the journal article from which the
# data were obtained.
#
data_2203138
loop_
_publ_author_name
'Guo, Ming-Lin'
_publ_section_title
;
 N-(4-Methyl-1-piperazinyl)phthalimide
;
_journal_issue                   2
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o306
_journal_page_last               o307
_journal_paper_doi               10.1107/S1600536804001825
_journal_volume                  60
_journal_year                    2004
_chemical_formula_iupac          'C13 H15 N3 O2'
_chemical_formula_moiety         'C13 H15 N3 O2'
_chemical_formula_sum            'C13 H15 N3 O2'
_chemical_formula_weight         245.28
_chemical_name_systematic
;
N-(4-methyl-1-piperazinyl)phthalimide
;
_space_group_IT_number           11
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2yb'
_symmetry_space_group_name_H-M   'P 1 21/m 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                90.00
_cell_angle_beta                 101.980(6)
_cell_angle_gamma                90.00
_cell_formula_units_Z            2
_cell_length_a                   8.364(3)
_cell_length_b                   6.816(3)
_cell_length_c                   10.972(5)
_cell_measurement_reflns_used    853
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      26.40
_cell_measurement_theta_min      2.80
_cell_volume                     611.9(4)
_computing_cell_refinement       SMART
_computing_data_collection       'SMART (Bruker 1997)'
_computing_data_reduction        'SAINT (Bruker 1997)'
_computing_molecular_graphics    SHELXTL
_computing_publication_material  SHELXTL
_computing_structure_refinement  SHELXTL
_computing_structure_solution    'SHELXTL (Sheldrick, 2001)'
_diffrn_ambient_temperature      293(2)
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device_type  'Bruker SMART CCD area-detector'
_diffrn_measurement_method       'φ and ω'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0214
_diffrn_reflns_av_sigmaI/netI    0.0245
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -8
_diffrn_reflns_number            3540
_diffrn_reflns_theta_full        26.41
_diffrn_reflns_theta_max         26.41
_diffrn_reflns_theta_min         1.90
_diffrn_standards_decay_%        0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.092
_exptl_absorpt_correction_T_max  0.985
_exptl_absorpt_correction_T_min  0.976
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(SADABS; Sheldrick, 1996)'
_exptl_crystal_colour            Colorless
_exptl_crystal_density_diffrn    1.331
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       Prism
_exptl_crystal_F_000             260
_exptl_crystal_size_max          0.24
_exptl_crystal_size_mid          0.22
_exptl_crystal_size_min          0.16
_refine_diff_density_max         0.222
_refine_diff_density_min         -0.140
_refine_ls_extinction_coef       0.30(2)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     SHELXL97
_refine_ls_goodness_of_fit_ref   1.075
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     112
_refine_ls_number_reflns         1372
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.075
_refine_ls_R_factor_all          0.0539
_refine_ls_R_factor_gt           0.0410
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w = 1/[σ²(Fo²)+(0.0616P)²+0.071P] where P = (Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1051
_refine_ls_wR_factor_ref         0.1138
_reflns_number_gt                1064
_reflns_number_total             1372
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            ac6078.cif
_cod_data_source_block           I
_cod_original_sg_symbol_H-M      'P 21/m'
_cod_database_code               2203138
_cod_database_fobs_code          2203138
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y+1/2, -z'
'-x, -y, -z'
'x, -y-1/2, z'
loop_
_atom_site_label
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_occupancy
_atom_site_type_symbol
O1 0.09160(17) 0.2500 0.53563(13) 0.0658(5) Uani d S 1 O
O2 0.33863(19) 0.2500 0.20035(13) 0.0656(5) Uani d S 1 O
N1 0.17519(19) 0.2500 0.34678(14) 0.0454(4) Uani d S 1 N
N2 0.01766(19) 0.2500 0.26989(15) 0.0459(4) Uani d S 1 N
N3 -0.2218(2) 0.2500 0.04513(14) 0.0498(5) Uani d S 1 N
C1 0.1975(2) 0.2500 0.47739(17) 0.0430(5) Uani d S 1 C
C2 0.3774(2) 0.2500 0.52412(17) 0.0387(4) Uani d S 1 C
C3 0.4669(2) 0.2500 0.64501(18) 0.0447(5) Uani d S 1 C
H3 0.4158 0.2500 0.7126 0.052(6) Uiso d SR 1 H
C4 0.6360(2) 0.2500 0.6615(2) 0.0481(5) Uani d S 1 C
H4 0.6997 0.2500 0.7418 0.050(6) Uiso d SR 1 H
C5 0.7113(2) 0.2500 0.5608(2) 0.0502(5) Uani d S 1 C
H5 0.8248 0.2500 0.5744 0.068(7) Uiso d SR 1 H
C6 0.6206(2) 0.2500 0.4402(2) 0.0494(5) Uani d S 1 C
H6 0.6717 0.2500 0.3725 0.052(6) Uiso d SR 1 H
C7 0.4526(2) 0.2500 0.42321(17) 0.0408(4) Uani d S 1 C
C8 0.3241(2) 0.2500 0.30737(18) 0.0460(5) Uani d S 1 C
C9 -0.01328(18) 0.0716(2) 0.19382(14) 0.0547(4) Uani d . 1 C
H9A 0.0051 -0.0435 0.2469 0.066(5) Uiso d R 1 H
H9B 0.0604 0.0657 0.1363 0.071(5) Uiso d R 1 H
C10 -0.18826(17) 0.0754(2) 0.12258(13) 0.0537(4) Uani d . 1 C
H10A -0.2094 -0.0404 0.0704 0.066(5) Uiso d R 1 H
H10B -0.2610 0.0722 0.1808 0.061(4) Uiso d R 1 H
C13 -0.3922(3) 0.2500 -0.0222(2) 0.0652(7) Uani d S 1 C
H13A -0.4127 0.3650 -0.0736 0.098 Uiso d R 1 H
H13B -0.4629 0.2500 0.0364 0.098 Uiso d SR 1 H
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle
C8 N1 C1 . . 112.11(15)
C8 N1 N2 . . 126.59(16)
C1 N1 N2 . . 121.30(15)
N1 N2 C9 . 4_565 111.91(9)
N1 N2 C9 . . 111.91(9)
C9 N2 C9 4_565 . 111.96(16)
C10 N3 C10 4_565 . 109.71(15)
C10 N3 C13 4_565 . 110.14(10)
C10 N3 C13 . . 110.14(10)
O1 C1 N1 . . 126.09(17)
O1 C1 C2 . . 128.73(18)
N1 C1 C2 . . 105.18(15)
C3 C2 C7 . . 121.57(17)
C3 C2 C1 . . 129.76(17)
C7 C2 C1 . . 108.67(16)
C2 C3 C4 . . 117.37(18)
C2 C3 H3 . . 121.2
C4 C3 H3 . . 121.4
C5 C4 C3 . . 121.15(19)
C5 C4 H4 . . 119.4
C3 C4 H4 . . 119.4
C4 C5 C6 . . 121.04(18)
C4 C5 H5 . . 119.5
C6 C5 H5 . . 119.5
C7 C6 C5 . . 118.08(19)
C7 C6 H6 . . 121.1
C5 C6 H6 . . 120.9
C6 C7 C2 . . 120.80(18)
C6 C7 C8 . . 130.69(18)
C2 C7 C8 . . 108.52(16)
O2 C8 N1 . . 125.20(19)
O2 C8 C7 . . 129.28(18)
N1 C8 C7 . . 105.52(16)
N2 C9 C10 . . 108.53(12)
N2 C9 H9A . . 110.0
C10 C9 H9A . . 109.9
N2 C9 H9B . . 110.1
C10 C9 H9B . . 110.0
H9A C9 H9B . . 108.3
N3 C10 C9 . . 111.41(13)
N3 C10 H10A . . 109.3
C9 C10 H10A . . 109.3
N3 C10 H10B . . 109.4
C9 C10 H10B . . 109.4
H10A C10 H10B . . 108.0
N3 C13 H13A . . 109.5
N3 C13 H13B . . 109.5
H13A C13 H13B . . 109.5
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_site_symmetry_2
_geom_bond_distance
O1 C1 . 1.195(2)
O2 C8 . 1.205(2)
N1 C8 . 1.401(2)
N1 C1 . 1.406(2)
N1 N2 . 1.409(2)
N2 C9 4_565 1.4672(17)
N2 C9 . 1.4672(17)
N3 C10 4_565 1.4554(18)
N3 C10 . 1.4554(18)
N3 C13 . 1.463(3)
C1 C2 . 1.486(2)
C2 C3 . 1.381(3)
C2 C7 . 1.382(3)
C3 C4 . 1.388(3)
C3 H3 . 0.9300
C4 C5 . 1.381(3)
C4 H4 . 0.9300
C5 C6 . 1.382(3)
C5 H5 . 0.9300
C6 C7 . 1.379(3)
C6 H6 . 0.9299
C7 C8 . 1.484(3)
C9 C10 . 1.5095(19)
C9 H9A . 0.9699
C9 H9B . 0.9700
C10 H10A . 0.9699
C10 H10B . 0.9699
C13 H13A . 0.9599
C13 H13B . 0.9600
loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_site_symmetry_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
C5 H5 O1 1_655 0.93 2.36 3.249(3) 161
C5 H5 O1 4_665 0.93 2.36 3.249(3) 161
loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_4
_geom_torsion
C8 N1 N2 C9 . 4_565 -63.29(11)
C1 N1 N2 C9 . 4_565 116.71(11)
C8 N1 N2 C9 . . 63.29(11)
C1 N1 N2 C9 . . -116.71(11)
C8 N1 C1 O1 . . 180.0
N2 N1 C1 O1 . . 0.0
C8 N1 C1 C2 . . 0.0
N2 N1 C1 C2 . . 180.0
O1 C1 C2 C3 . . 0.0
N1 C1 C2 C3 . . 180.0
O1 C1 C2 C7 . . 180.0
N1 C1 C2 C7 . . 0.0
C7 C2 C3 C4 . . 0.0
C1 C2 C3 C4 . . 180.0
C2 C3 C4 C5 . . 0.0
C3 C4 C5 C6 . . 0.0
C4 C5 C6 C7 . . 0.0
C5 C6 C7 C2 . . 0.0
C5 C6 C7 C8 . . 180.0
C3 C2 C7 C6 . . 0.0
C1 C2 C7 C6 . . 180.0
C3 C2 C7 C8 . . 180.0
C1 C2 C7 C8 . . 0.0
C1 N1 C8 O2 . . 180.0
N2 N1 C8 O2 . . 0.0
C1 N1 C8 C7 . . 0.0
N2 N1 C8 C7 . . 180.0
C6 C7 C8 O2 . . 0.0
C2 C7 C8 O2 . . 180.0
C6 C7 C8 N1 . . 180.0
C2 C7 C8 N1 . . 0.0
N1 N2 C9 C10 . . 175.38(12)
C9 N2 C9 C10 4_565 . -58.1(2)
C10 N3 C10 C9 4_565 . -58.3(2)
C13 N3 C10 C9 . . -179.75(14)
N2 C9 C10 N3 . . 57.70(17)
